Pinobanksin

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  • Identifiers

    CAS number
    548-82-3

    Molecular formula
    C15H12O5

    SMILES
    C1=CC=C(C=C1)[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O

    Safety labels

  • Odor profile

    Fragrance
    Odorless 60.4%
    Phenolic 45.08%
    Sweet 30.25%
    Spicy 29.66%
    Vanilla 28.43%
    Bitter 26.11%
    Burnt 24.21%
    Balsamic 24.05%
    Medicinal 19.66%
    Smoky 19.51%

     

    Flavor
    Bitter 91.82%
    Sweet-like 21.19%
    Odorless 21.09%
    Lovage 20.73%
    Cedarleaf 20.58%
    Bland 20.09%
    Nitrile 19.69%
    Parsley 19.57%
    Ethyl benzoate 19.13%
    Ripe apricot 19.07%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.2

    pKa est.
    9.08 (weak base)

    Molecular weight
    272.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    599°C

    Flash point

    • 221.84 ˚C est.

  • Synonyms

    • Pinobanksin
    • 548-82-3
    • 3,5,7-Trihydroxyflavanone
    • (2R,3R)-pinobanksin
    • BK3ABR33DT
    • (2R,3R)-3,5,7-trihydroxy-2-phenyl-2,3-dihydrochromen-4-one
    • 2,3-Dihydro-3,5,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
    • (2R,3R)-3,5,7-Trihydroxy-2-phenyl-chroman-4-one
    • CHEBI:28103
    • DTXSID10203287
    • RefChem:929305
    • GlyTouCan:G86754PD
    • 3,5,7-trihydroxy-flavanone
    • DTXCID10125778
    • G86754PD
    • Pinobaksin
    • MFCD07784478
    • (2r,3r)-3,5,7-trihydroxy-2-phenyl-2,3-dihydro-4h-chromen-4-one
    • CHEMBL608410
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-phenyl-,(2R,3R)-
    • (2R,3R)-2,3-dihydro-3,5,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
    • (2R,3R)-2,3-Dihydro-3,5,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one; (2R-trans)-2,3-Dihydro-3,5,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one; 3,5,7-Trihydroxyflavanone; (2R,3R)-Pinobanksin; 3,5,7-Trihydroxyflavanone; Dihydrogalangin
    • 3,5,7-Trihydroxyflavanone; Dihydrogalangin
    • (2R,3R)-3,5,7-Trihydroxyflavanone
    • UNII-BK3ABR33DT
    • (2R,3R)-3,5,7-Trihydroxy-2-phenylchroman-4-one
    • MEGxp0_001314
    • orb2813875
    • SCHEMBL1045054
    • ACon1_000534
    • Pinobanksin, >=95% (HPLC)
    • HY-N3062
    • BDBM50304071
    • (2R,3R)-3,5,7-trihydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
    • AKOS032948403
    • NCGC00168987-01
    • DA-76895
    • PS-12128
    • CS-0023135
    • C09826
    • E87105
    • Q953294
    • (2R,3R)-3,5,7-Trihydroxy-2-phenyl-chroman-4-one;
    • BRD-K52291974-001-01-7
    • 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-phenyl-
    • (2R,3R)-3,5,7-Trihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
    • 4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-3,5,7-TRIHYDROXY-2-PHENYL-, (2R,3R)-
    • 548-82-3

  • Applications

    Pinobanksin, CAS 548-82-3, is a natural flavonoid present in honey and propolis; in industry it is commonly evaluated as an antioxidant and considered as a marker compound for quality control in bee-derived products, used as an intermediate in the synthesis of flavonoid derivatives in pharmaceutical research, explored for cosmetic formulations as an antioxidant active ingredient in skin-care products, and investigated as a potential nutraceutical component; it is also used as a reference standard in analytical methods for honey, propolis, and related natural products.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 18.11
    methanol 87.15
    isopropanol 54.27
    water 0.14
    ethyl acetate 43.52
    n-propanol 33.46
    acetone 214.41
    n-butanol 34.64
    acetonitrile 61.68
    DMF 390.68
    toluene 4.0
    isobutanol 23.97
    1,4-dioxane 74.21
    methyl acetate 49.14
    THF 470.21
    2-butanone 96.9
    n-pentanol 25.13
    sec-butanol 30.51
    n-hexane 0.12
    ethylene glycol 57.77
    NMP 169.63
    cyclohexane 0.28
    DMSO 2068.93
    n-butyl acetate 21.26
    n-octanol 14.61
    chloroform 2.46
    n-propyl acetate 26.47
    acetic acid 60.66
    dichloromethane 2.05
    cyclohexanone 94.01
    propylene glycol 52.85
    isopropyl acetate 33.01
    DMAc 337.93
    2-ethoxyethanol 96.15
    isopentanol 36.53
    n-heptane 0.41
    ethyl formate 33.68
    1,2-dichloroethane 9.18
    n-hexanol 22.87
    2-methoxyethanol 265.07
    isobutyl acetate 11.54
    tetrachloromethane 0.97
    n-pentyl acetate 13.46
    transcutol 171.21
    n-heptanol 12.86
    ethylbenzene 2.52
    MIBK 43.75
    2-propoxyethanol 91.82
    tert-butanol 82.27
    MTBE 19.19
    2-butoxyethanol 38.19
    propionic acid 33.29
    o-xylene 4.32
    formic acid 54.15
    diethyl ether 16.29
    m-xylene 4.54
    p-xylene 3.14
    chlorobenzene 3.67
    dimethyl carbonate 46.47
    n-octane 0.23
    formamide 134.23
    cyclopentanone 189.01
    2-pentanone 87.28
    anisole 15.82
    cyclopentyl methyl ether 53.39
    gamma-butyrolactone 151.26
    1-methoxy-2-propanol 225.51
    pyridine 28.64
    3-pentanone 44.67
    furfural 82.06
    n-dodecane 0.54
    diethylene glycol 123.14
    diisopropyl ether 5.43
    tert-amyl alcohol 39.54
    acetylacetone 124.41
    n-hexadecane 0.63
    acetophenone 24.7
    methyl propionate 54.25
    isopentyl acetate 18.87
    trichloroethylene 15.23
    n-nonanol 14.08
    cyclohexanol 30.68
    benzyl alcohol 21.18
    2-ethylhexanol 13.34
    isooctanol 10.66
    dipropyl ether 14.29
    1,2-dichlorobenzene 4.38
    ethyl lactate 35.2
    propylene carbonate 45.55
    n-methylformamide 154.54
    2-pentanol 27.81
    n-pentane 0.17
    1-propoxy-2-propanol 66.14
    1-methoxy-2-propyl acetate 49.08
    2-(2-methoxypropoxy) propanol 51.64
    mesitylene 3.46
    ε-caprolactone 57.28
    p-cymene 4.32
    epichlorohydrin 132.62
    1,1,1-trichloroethane 5.99
    2-aminoethanol 61.5
    morpholine-4-carbaldehyde 139.35
    sulfolane 303.19
    2,2,4-trimethylpentane 0.36
    2-methyltetrahydrofuran 73.65
    n-hexyl acetate 21.52
    isooctane 0.36
    2-(2-butoxyethoxy)ethanol 67.25
    sec-butyl acetate 16.46
    tert-butyl acetate 36.48
    decalin 0.42
    glycerin 138.47
    diglyme 115.34
    acrylic acid 38.53
    isopropyl myristate 10.92
    n-butyric acid 44.62
    acetyl acetate 26.39
    di(2-ethylhexyl) phthalate 12.31
    ethyl propionate 25.92
    nitromethane 216.1
    1,2-diethoxyethane 31.0
    benzonitrile 17.11
    trioctyl phosphate 11.21
    1-bromopropane 2.92
    gamma-valerolactone 176.5
    n-decanol 10.88
    triethyl phosphate 14.65
    4-methyl-2-pentanol 17.86
    propionitrile 41.07
    vinylene carbonate 31.49
    1,1,2-trichlorotrifluoroethane 98.47
    DMS 25.4
    cumene 2.28
    2-octanol 9.5
    2-hexanone 38.85
    octyl acetate 14.26
    limonene 6.43
    1,2-dimethoxyethane 138.6
    ethyl orthosilicate 12.39
    tributyl phosphate 12.73
    diacetone alcohol 102.61
    N,N-dimethylaniline 12.84
    acrylonitrile 62.91
    aniline 15.71
    1,3-propanediol 98.77
    bromobenzene 2.34
    dibromomethane 1.34
    1,1,2,2-tetrachloroethane 17.77
    2-methyl-cyclohexyl acetate 16.06
    tetrabutyl urea 20.88
    diisobutyl methanol 10.35
    2-phenylethanol 22.9
    styrene 2.47
    dioctyl adipate 17.28
    dimethyl sulfate 101.79
    ethyl butyrate 19.75
    methyl lactate 85.87
    butyl lactate 22.4
    diethyl carbonate 14.03
    propanediol butyl ether 46.69
    triethyl orthoformate 17.09
    p-tert-butyltoluene 4.24
    methyl 4-tert-butylbenzoate 27.41
    morpholine 114.67
    tert-butylamine 17.27
    n-dodecanol 8.19
    dimethoxymethane 212.23
    ethylene carbonate 30.16
    cyrene 54.99
    2-ethoxyethyl acetate 23.03
    2-ethylhexyl acetate 12.57
    1,2,4-trichlorobenzene 7.6
    4-methylpyridine 27.99
    dibutyl ether 11.38
    2,6-dimethyl-4-heptanol 10.35
    DEF 78.09
    dimethyl isosorbide 80.63
    tetrachloroethylene 9.37
    eugenol 29.49
    triacetin 29.19
    span 80 32.12
    1,4-butanediol 34.08
    1,1-dichloroethane 4.85
    2-methyl-1-pentanol 20.74
    methyl formate 106.94
    2-methyl-1-butanol 25.5
    n-decane 0.79
    butyronitrile 33.11
    3,7-dimethyl-1-octanol 13.7
    1-chlorooctane 4.26
    1-chlorotetradecane 2.08
    n-nonane 0.55
    undecane 0.65
    tert-butylcyclohexane 0.37
    cyclooctane 0.2
    cyclopentanol 47.6
    tetrahydropyran 43.52
    tert-amyl methyl ether 18.04
    2,5,8-trioxanonane 91.4
    1-hexene 0.89
    2-isopropoxyethanol 54.7
    2,2,2-trifluoroethanol 29.6
    methyl butyrate 37.38

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction